Sheffield, Massachusetts Vacation Rentals

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Massachusetts

$560.20

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Massachusetts

$560.20

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Massachusetts

$560.20

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Massachusetts

$623.66

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Massachusetts

$560.20

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Massachusetts

$560.20

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Massachusetts

$560.20

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Massachusetts

$560.20

Waterview Home in the Berkshires: Near Hiking

Massachusetts

$324.21

Waterview Home in the Berkshires: Near Hiking

Massachusetts

$324.21

Skiing & Hiking: Water-View Home in the Berkshires

Massachusetts

$324.21

Skiing & Hiking: Water-View Home in the Berkshires

Massachusetts

$312.09

Skiing & Hiking: Water-View Home in the Berkshires

Massachusetts

$309.43

Skiing & Hiking: Water-View Home in the Berkshires

Massachusetts

$310.68

Cheerful 3-bedroom cottage with woodstove

Massachusetts

$217.00

Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT

Massachusetts

$450.00

Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT

Massachusetts

$450.00

Luxury Berkshire Estate: Proximity to all the best the Berkshires has to offer!

Massachusetts

$0.00

Luxury Berkshire Estate: Proximity to all the best the Berkshires has to offer!

Massachusetts

$2442.24

Luxury Berkshire Estate: Proximity to all the best the Berkshires has to offer!

Massachusetts

$2442.24